


Popping The Anal Cherry

by thegreatficmaster



Series: Supernatural Collection [52]
Category: Supernatural
Genre: Anal Sex, F/M, Reader-Insert, Smut
Language: English
Status: Completed
Published: 2019-07-18
Updated: 2019-07-18
Packaged: 2020-07-07 19:31:08
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,818
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19856854
Author URL: https://archiveofourown.org/users/thegreatficmaster/pseuds/thegreatficmaster
Summary: Y/n and Dean give into lust, Y/n allowing him to be her first in a different way.





	Popping The Anal Cherry

“Seriously, Dean? I told you we should have got Sam with us instead of leaving him at the damn motel!”

Dean rolled his eyes, trying to focus on getting to the other side of the house and burning the damn doll the mother attached herself to, once her child died.

Looking around, he searched for the ghost, not seeing her at all.

Thinking this was his chance, he sprinted forward, only getting halfway there when she appeared again, throwing him against the wall before he had the chance to react.

Y/n rushed forward, seeing this as her chance and grabbed the creepy ass doll, setting it ablaze and watching as the ghost burst into flames, disappearing and leaving y/n to sort out the damn Winchester.

She walked over to him, inspecting his head, making sure there was no bleeding or any bumps.

Running her hands through his hair, she noticed the way he relaxed, shutting his eyes and sighing.

She continued this for a while, wanting to give Dean some peace, even if it was just for a few minutes.

Suddenly, he grabbed her hand, pulling her down and kissing her hard.

She stayed there, her lips attached to his, completely frozen in shock.

Never would she have thought Dean Winchester, the most beautiful man ever, would want her.

He pulled back when he felt her tense up, thinking this was all a big mistake.

“Shit, y/n. I’m so sorry. I just-I…”

His sentence was left unfinished as she connected their lips again, loving the feel of the strangely soft lips against hers, the scruff on his face rubbing and tickling her.

She ran her fingers through his hair, her other hand gripping onto his shoulder as he grabbed her waist, flipping them and laying her down on the dusty floor.

He spread her legs and placed himself between them, y/n jerking her hips up in an attempt to rub against Dean’s crotch, needing some sort of friction, her pussy throbbing with the need to be filled.

“Patience, baby”.

Y/n felt her panties getting a whole lot more wet at the pet name, loving the sound of it when it was being aimed at her, instead of that ugly ass car.

“Please, Dean. I need you inside me. Now”.

He chuckled, moving back and removing his clothes, y/n doing the same, shimmying out of her jeans and panties, ripping her shirt off and throwing her bra across the room.

Dean stared at her body. It was perfect.

She had huge breasts, but he knew they were real, unlike the women he used to sleep with. 

Hell, the only other woman who had real ones was Cassie, even Lisa having gotten fake ones at some point. 

The fake ones looked good and perky. 

But the real ones? Well, they were rare nowadays. And y/n’s ones were beyond perfect.

Y/n sat there, letting Dean appreciate her body, doing the same to him.

He was perfect.

His body wasn’t as muscular as Sam’s. 

But y/n always thought Sam’s body was kinda gross. 

Too much muscle. It just looked strange.

But Dean had the muscle, along with a little bit of pudginess. 

He wasn’t fat, just a little softer around the edges. 

That was what y/n always liked. 

She couldn’t help but appreciate his cock either.

He was thick. Really thick. 

Just a little over average in terms of length, but the girth of it. 

Y/n was sure Dean would stretch her more than ever before, and she couldn’t wait for it.

“Your pussy is so wet. Look, you’re literally dripping”.

Y/n looked down, seeing the trail of slick leaking from her pussy, leaving a dark patch on the floor.

She looked up to see Dean lick his lips in hunger, leaving them glistening.

Y/n bit her lip, wanting it to be her tongue that ran over his lips.

She leaned forward, deciding to be the one to be in charge and gripped the back of his neck.

Staring into his eyes for a few seconds, she saw his pupils completely blown with lust, sure hers were too.

She jumped onto him, pushing him onto the floor as she sat on his chest, her tongue invading his mouth as she rubbed herself on him, his abs and nipples giving her the little friction she was seeking. 

It wasn’t enough, but for now, she needed to taste his mouth as she left her wetness all over his chest.

She began going lower, peppering kisses along his jaw and neck, sucking and biting, lowering herself as she licked his chest, tasting the sweat that had built up from the hunt, along with her own juices, the mix of the saltiness and the tang being a strange, yet delicious taste.

She lowered herself until her face was hovering above his cock, almost touching her lips, shining with the precum, red and straining to be touched.

“What do you want, Dean? Tell me”, she whispered, tracing patterns in his bush.

“Suck my cock. Suck it hard. Make me blow in that pretty mouth”.

She smiled, gripping his cock with both hands as he licked his lips in anticipation.

Y/n caught sight of the pink, wet tongue, wanting it inside her pussy as Dean ate her out.

She lowered her head, kissing his swollen tip and pulling back, the precum creating a string to her mouth.

Licking her lips, she got a taste of what she’d soon be swallowing down.

She expected Dean’s cum to taste gross, but it tasted good. 

Really good. Less salty than other guys she’d been with.

She took his length into her mouth, half of it in, the other half held by one hand as the other squeezed his balls.

She sucked, licking at his shaft and slightly scraping her teeth on it, simultaneously wanking it as well while she fondled his balls.

His hand gripped her hair, the other tucked behind his head as he shut his eyes, his lower lip caught between his teeth.

“Fuck, y/n. Don’t fucking stop. Suck that fat cock. You like it? Hmm? Like my big fat cock inside your pretty little mouth?”

Y/n usually would’ve rolled her eyes when guys boasted about the size of their dick, more often than not exaggerating. 

But Dean was right. 

His cock was thick as fuck, her mouth stretching as though she was at the damn dentist.

She let him take control, feeling the way his grip tightened on her hair, knowing he wanted to fuck her face.

He gripped her hair with both hands, thrusting into her mouth hard and fast, y/n holding onto his thick thighs, her nails digging in as she gagged and choked on his cock.

“Fuck! You look so good with my cock disappearing into your mouth. I’d love to see you looking like this more often”, he grunted.

Y/n groaned, his words, along with the taste of his cock and the sweat from the hunt, making her hornier than ever.

He continued his brutal pace, hitting the back of her throat each time he thrust in, y/n having to supress her gag reflex as tears and drool collected on his balls and stomach.

“Play with that sweet pussy, sweetheart”.

Y/n would’ve let out a sigh of relief had her mouth not been occupied by Dean’s cock, her pussy throbbing, needing to be touched.

She reached down with her right hand, pressing her index finger against her clit and immediately jolting, the sensation being overwhelming.

“Fuck, sweetheart. Don’t jump like that”.

Y/n nodded, his cock still in her mouth as he resumed his thrusts, y/n slowly pressing down on the bundle and gradually rubbing faster and faster, until her pussy was dripping with her arousal.

She easily slipped in two fingers, fucking herself with them as she stroked her sweet spot, feeling her walls tightening.

“You close, sweetheart? Gonna cum for me? Do it! Cum all over those fingers for me”.

Y/n let out a muffled scream, her walls clamping down on her slender fingers as her toes curled, her juices coating her hand and dripping down onto the floor.

In the midst of her orgasm, Dean’s thrusts faltered, y/n slightly biting as her orgasm washed over her body.

He yelled out in shock, instantly cumming, releasing rope after rope of his hot load down her throat.

Y/n was caught off guard, not swallowing any until most of it fell out of her mouth, gulping down the few drops that remained.

They both came down from their highs, Dean breathing heavily with his arms thrown across his head, y/n holding onto Dean’s thighs as she caught her breath.

“Lick it up”.

Y/n looked up at the man, sweaty and panting, confused as to what he meant.

“Lick it up. This".

He pointed to the puddle of spit and cum on his stomach, slightly streaking down his sides, leaving behind a shiny, sticky trail.

She immediately leaned down, scrunching her hair into a ponytail and slurping it all up, not swallowing it as she let the flavours wash over her taste buds.

“Feed it to me”.

Y/n felt her pussy clench.

Usually, most guys wouldn’t even be willing to kiss after a blow job, their masculinity too threatened. 

But here was Dean Winchester, one of the most alpha males she’d met, willingly asking her to feed him the mixture of her spit and his cum.

She climbed onto his chest, leaning down and opening her mouth, letting the fluids slide out of her mouth and drop into his.

“Fingers”, he mumbled to her, grabbing her soaked hand and sticking her fingers into his mouth.

A filthy moan erupted from him, y/n feeling the rumbling against her pussy.

He loved the taste of her spit, his cum and then the added flavour of hers too.

This was by far his favourite meal.

He swallowed it all down, gripping her arms and pulling her down into a messy, wet, sloppy kiss, leaving behind the remaining mixture all over her lips and tongue, y/n swallowing down the taste too.

“Get on top of me, sweetheart. Gonna fuck that pussy good. Gonna fill it all the way up”.

Y/n quivered in anticipation, shuffling down as she rubbed her pussy against his cock, leaving behind her slick, knowing she was going to be stretched like hell.

“God, Dean. Fuck!”

He chuckled when he saw the look on her face, her mouth slightly parted and her hands back, holding onto his thighs as she just looked up to the ceiling, her eyes scrunched closed.

She was so beautiful. It was beyond anything he could have ever imagined.

He leaned up, holding himself on his arms as he took a nipple in his mouth.

Her eyes opened and she looked down at him, placing an arm on his shoulder to steady herself, the other scratching at his hair lightly.

He was an expert with his mouth, the way he rolled her nipple, tugging on it with his teeth as he suckled, paying attention to both breasts.

Pushing his head further into her breasts, y/n reached down and gripped Dean’s cock, lining it up with her entrance and sinking down slowly, letting her walls accommodate his size, adjusting and relaxing.

“You gonna move, sweetheart? Or we gonna sit here all day?”

Y/n scowled at the dumb smirk on his face, lifting herself and slamming back down, his fat cock hitting her g-spot immediately.

Dean’s smirk fell off his face, his mouth hanging open. 

Never had he had a pussy so tight or wet before, warming his cock like no other.

Y/n smiled at his reaction, lifting herself again and slamming back down.

“Fuck, sweetheart. Keep going. Fuck yourself on my fat cock”.

Y/n happily obliged, slamming herself down as Dean thrusted up, her hands gripping his head as close to her as she could, the pleasure being too much, needing an anchor to tie her down.

He slipped out a few times, having to realign himself.

The third time it happened, he pushed his cock back in, y/n letting out a yelp.

“What the fuck, Dean! That’s my ass”, she hissed in pain, never having done anal before.

“Shit. I’m so sorry”.

“Wait”, she stopped him from pulling out, liking the feeling of him in her other hole.

“Fuck my ass, Dean”.

Dean had an excited smile on him, giddy at the thought of finally doing anal, none of the previous women having been willing to try.

“Ok, sweetheart. Get ready”.

He flipped them, y/n now laying on her back as Dean sat on his knees, his cock still buried inside her ass. 

It was tighter than her pussy, if that was even possible.

Dean pulled back, hearing y/n hiss, then thrust back in.

“Fuuckkk!!”

“Gonna fuck you hard and fast, sweetheart. Make that ass loose, let me slide right into there from now on”.

He began pounding into her, y/n gripping his biceps as she licked his neck and chest, collecting up the sweat that had built up, loving the taste of him.

“Fuck, sweetheart. This ass is so tight. You feel me inside you? Huh? Feel this big fat cock stretching that tight hole? That’s what I’m gonna do all the time from now on! Gonna stretch out that hole nice and good”. 

Y/n pleaded with him, begging him to do it, stretch her ass and fuck her hard.

Dean continued his pace, biting onto her nipples and chest, leaving behind marks, her entire upper body littered with teeth indentations and bruises, Dean having the same.

“Fuck! Need to taste this pussy”, he declared, seeing the fluids running down onto his cock.

He pulled out of her ass, leaning down and throwing her legs over his shoulders.

He stuck his tongue in, rapidly going in and out, nibbling on her clit slightly and lapping at her pussy.

“Fuck, y/n. This cunt tastes so sweet. Can’t believe we waited until now to do this”.

He moaned and spoke into her pussy, the vibrations spreading through her body, pulling his hair a bit too hard, feeling a few tears falling from his eyes.

He stopped eating her after a few minutes, his face shining with her juices. 

He held onto the base of his cock, slapping her pussy with it a few times, hitting her clit and seeing her squirm and buck her hips, needing him inside her again.

“Stop being such a fucking tease, Dean. Get inside me and fuck me. Now!”

“As you wish, ma’am”.

He plunged his cock inside her, pounding into her as she slid on the dusty floor, her back dirty and scraping against it.

“Oh my god. Fuck, Dean, I’m so close”, y/n breathed out.

“Play with that pussy again for me. Make yourself cum on my cock. Soak my fat dick, baby”.

Y/n rubbed at her clit, Dean inserting a finger in along with his cock, stroking at her g-spot constantly.

The feeling of Dean’s sweaty body on top of her, his sweat dripping down from his forehead into her mouth, the way his fat cock stretched her walls along with his finger, filling her up and the sensation of him biting on her nipples every few seconds, overwhelmed her.

Her vision went white, her back arching into his chest as she screamed louder than ever before, clawing at his shoulders, needing something to ground her down, afraid she’d die from the strength of her orgasm.

Dean came as her pussy clamped down, cumming deep inside her, before a force made him pull out, a gush of liquid flowing out of her pussy, his cum mixing with it.

Dean stared at it in shock. 

He’d never made a woman squirt before. Not like this.

He leaned down, inserting his finger and his tongue, pumping them in and out as he worked her through her orgasm, tasting the mixture of their cum, the saltiness and tanginess even more pronounced this time.

They were left panting and wordless, y/n coming back around as Dean lay beside her, grabbing her small body and holding her to his chest.

“That was-just-I mean…”

He chuckled, nodding along with her, unable to say anything himself.

He placed a kiss in her hair, inhaling her scent, the strawberry mixed with the smell of sweat and dust. But it was still heavenly.

They’d discuss where their relationship would go later, both of them hoping this would become more, hoping they’d belong to each other. 

But for now, they’d just lay there, in each other’s embrace, sleeping in the arms of the ones they’d always wanted, but never thought they’d have. 


End file.
